7189-05-1Relevant academic research and scientific papers
The use of enaminones and enamines as effective synthons for MSA-catalyzed regioselective synthesis of 1,3,4-tri- And 1,3,4,5-tetrasubstituted pyrazoles
Duan, Liancheng,Zhou, Hui,Gu, Yucheng,Gong, Ping,Qin, Mingze
, p. 16131 - 16137 (2019/11/03)
In the present work, an efficient regioselective synthesis of 1,3,4-tri- and 1,3,4,5-tetrasubstituted pyrazoles via a methanesulfonic acid (MSA)-catalyzed reaction of hydrazones with enaminones or enamines is reported. Mechanistically, the formation of the title compounds involves the [2+3] cycloaddition of hydrazones with enaminones or enamines followed by aromatization with acid and oxygen. This convenient method under mild conditions with various hydrazones, enaminones, and enamines was well-tolerated to afford products in good to excellent yields. Compared with the literature methods, this strategy has advantages such as materials that are available economically, metal-free catalysis, excellent regioselectivity, and high efficiency.
Synthesis of 3-substituted 1-phenyl-1H-pyrazole-4-carbaldehydes and the corresponding ethanones by Pd-catalysed cross-coupling reactions
Arbaciauskiene, Egle,Martynaitis, Vytas,Krikstolaityte, Sonata,Holzer, Wolfgang,Sackus, Algirdas
, p. 1 - 21 (2012/02/04)
An efficient synthetic route to construct ortho-substituted 1-phenyl-1H-pyrazole-4-carboxaldehydes and the corresponding ethanones starting from 1-phenyl-1H-pyrazol-3-ol is described. Carbon-carbon bond-forming Pd-catalysed cross-coupling reactions were applied for the functionalisation of the intermediate pyrazole triflates. Detailed NMR spectroscopic investigations were undertaken with all obtained products. ARKAT-USA, Inc.
1,3-Dipolar Cycloadditions of Aryl Nitrilimines to Electron-poor Alkenes
Adembri, Giorgio,Celli, Angela M.,Scotton, Mirella
, p. 249 - 251 (2007/10/02)
The 1,3-dipolar cycloadditions of aryl nitrilimines to 1,2-diacetylethylene gave along with 1,2-diaryl-4,5-diacetyl-4,5-dihydropyrazoles 5 and the corresponding dehydrogenated pyrazoles 6, the unexpected 1,3-diaryl-4-acetylpyrazoles 7.As for tetrasubstituted alkenes, whereas 1,2-diacetyl-1,2-dicarbethoxyethylene gave a stable cycloadduct 8, 1,2,3,4-tetraacetylethylene yielded a mixture of pyrazoles 6 and 7.
